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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): m72.
Published online 2009 December 16. doi:  10.1107/S1600536809053124
PMCID: PMC2980016

Tris[2-meth­oxy-6-(4-methyl­phenyl­iminio­meth­yl)phenolato-κ2 O,O′]tris­(thio­cyanato-κN)neodymium(III)

Abstract

In the title compound, [Nd(NCS)3(C15H15NO2)3], the NdIII ion is coordinated by three thio­cyanate anions [Nd—N = 2.489 (8)–2.530 (7) Å] and six O atoms [Nd—O = 2.375 (4)–2.843 (5) Å] from three zwitterionic 2-meth­oxy-6-(4-methyl­phenyl­iminiometh­yl)phenolate ligands in a tricapped trigonal-prismatic geometry. Intra­molecular N—H(...)O hydrogen bonds occur. The crystal packing exhibits weak inter­molecular C—H(...)S hydrogen bonds, π–π inter­actions with a distance of 3.904 (7) Å between the centroids of the aromatic rings, and voids of 101 Å3.

Related literature

For related structures, see: Wang & Chang (1994 [triangle]); Zhao et al. (2007 [triangle]); Xian et al. (2008 [triangle]); Li et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-00m72-scheme1.jpg

Experimental

Crystal data

  • [Nd(NCS)3(C15H15NO2)3]
  • M r = 1042.35
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-00m72-efi1.jpg
  • a = 16.6107 (3) Å
  • b = 14.2425 (3) Å
  • c = 22.1582 (4) Å
  • β = 105.972 (1)°
  • V = 5039.77 (17) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.21 mm−1
  • T = 296 K
  • 0.14 × 0.08 × 0.05 mm

Data collection

  • Bruker APEXII diffractometer
  • 44769 measured reflections
  • 11604 independent reflections
  • 5189 reflections with I > 2σ(I)
  • R int = 0.114

Refinement

  • R[F 2 > 2σ(F 2)] = 0.060
  • wR(F 2) = 0.190
  • S = 0.86
  • 11604 reflections
  • 562 parameters
  • H-atom parameters constrained
  • Δρmax = 0.66 e Å−3
  • Δρmin = −0.84 e Å−3

Data collection: APEX2 (Bruker, 2006 [triangle]); cell refinement: SAINT (Bruker, 2006 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809053124/cv2653sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053124/cv2653Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

Schiff base ligands derived from substituted salicylaldehyde and their metal complexes have been widely investigated because of their structural features (Wang et al.,1994). In this aspect we have been synthesized several analogous Schiff bases transitional and rare metal complexes. In recent articles we have reported our research results (Zhao et al., 2007; Xian et al., 2008; Li et al., 2008). Herein, we report the crystal structure of the title Nd3+ complex, (I).

In (I) (Fig. 1), the NdIII is nine- coordinated by three nitrogen atoms from three thiocyanate ions and six O atoms from 2-(4-methylphenyliminomethyl)-6-methoxyphenolato) (L). L ligands coordinate the Nd center with bidentate-chelate mode using oxygen atoms from deprotonated phenolic hydroxyl groups and methoxyl groups. The imino H atoms in L are involved in intramolecular N—H···O hydrogen bonds (Table 1). The bonds between NdIII and O atoms from phenolic hydroxyl groups are 2.375 (2) -2.393 (3) Å, which are shorter than those between Nd and O atoms of methoxyl groups (2.742 (3) - 2.843 (3) Å). The Nd—N bond lengths are 2.489 (4) -2.530 (4) Å. The structure of (I) is similar to the structures of analogous complexes (Zhao et al., 2007; Li et al., 2008).

The crystal packing exhibits weak intermolecular C—H···S hydrogen bonds (Table 1) and π-π interaction with the distance of 3.904 (7) Å between the centroids of aromatic rings.

Experimental

Reagents and solvents were of commercially available quality and were used without further purification. The Schiff base ligand was prepare in a high yield synthesis by condensation of o-vanillin and p-methyllaniline and was recrystallized in ethanol before being used. 1 mmol N d(NO3)3 (dissolved in methanol) was added dropwise into a methanol solution with 3 mmol 3-methoxy-N-salicylidene-p-toluidine under stirring and the mixture was continuously stirred at room temperature for 8 h to obtain a red solution. The deposit was filtered off and the solution was left standing for slow evaporation. Red crystals of the title compound were obtained after several days.

Refinement

All H atoms were positioned geometrically (C—H 0.93–0.96 Å, N—H 0.86 Å), and refined as riding, with Uiso(H) = 1.2–1.5Ueq(C, N). The crystal packing exhibits voids of 101 Å3 centered at (0.19, 0.67, 0.24).

Figures

Fig. 1.
The molecular structure of the title complex, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms omitted for clarity.

Crystal data

[Nd(NCS)3(C15H15NO2)3]F(000) = 2124
Mr = 1042.35Dx = 1.374 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2091 reflections
a = 16.6107 (3) Åθ = 1.4–27.6°
b = 14.2425 (3) ŵ = 1.21 mm1
c = 22.1582 (4) ÅT = 296 K
β = 105.972 (1)°Block, red
V = 5039.77 (17) Å30.14 × 0.08 × 0.05 mm
Z = 4

Data collection

Bruker APEXII diffractometer5189 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.114
graphiteθmax = 27.6°, θmin = 1.3°
ω scansh = −21→21
44769 measured reflectionsk = −18→18
11604 independent reflectionsl = −28→28

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.190H-atom parameters constrained
S = 0.86w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
11604 reflections(Δ/σ)max = 0.001
562 parametersΔρmax = 0.66 e Å3
0 restraintsΔρmin = −0.84 e Å3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Nd1.21267 (2)0.27661 (3)1.393189 (17)0.04942 (15)
C11.7474 (6)0.2005 (8)1.6278 (6)0.132 (4)
H1B1.79700.19351.61400.197*
H1C1.75170.16161.66390.197*
H1D1.74160.26491.63860.197*
C21.6709 (6)0.1709 (6)1.5751 (5)0.090 (3)
C31.6775 (5)0.1410 (7)1.5180 (6)0.098 (3)
H3B1.73030.13681.51150.118*
C41.6086 (5)0.1167 (6)1.4699 (4)0.079 (2)
H4A1.61500.09691.43150.095*
C51.5300 (5)0.1220 (5)1.4793 (4)0.064 (2)
C61.5214 (5)0.1515 (5)1.5365 (4)0.066 (2)
H6A1.46860.15521.54300.079*
C71.5906 (6)0.1754 (6)1.5834 (4)0.082 (2)
H7A1.58420.19511.62180.099*
C81.4479 (5)0.0514 (5)1.3821 (4)0.065 (2)
H8A1.49390.01821.37720.078*
C91.3712 (5)0.0448 (5)1.3347 (4)0.069 (2)
C101.3636 (7)−0.0112 (6)1.2797 (5)0.097 (3)
H10A1.4097−0.04481.27520.116*
C111.2900 (8)−0.0158 (8)1.2340 (5)0.110 (4)
H11A1.2860−0.05311.19880.132*
C121.2212 (7)0.0342 (7)1.2392 (4)0.096 (3)
H12A1.17130.03071.20730.115*
C131.2253 (5)0.0892 (5)1.2909 (4)0.066 (2)
C141.3004 (5)0.0943 (5)1.3399 (4)0.0613 (19)
C151.0798 (5)0.1339 (7)1.2583 (4)0.098 (3)
H15A1.07910.08221.23040.147*
H15B1.06420.19041.23440.147*
H15C1.04080.12211.28230.147*
C160.9337 (6)0.8193 (6)1.4168 (4)0.092 (3)
H16A0.98160.84871.40850.138*
H16B0.92890.83931.45700.138*
H16C0.88410.83681.38480.138*
C170.9441 (5)0.7145 (5)1.4168 (3)0.0619 (19)
C180.8840 (5)0.6555 (6)1.4276 (4)0.069 (2)
H18A0.83600.68091.43480.083*
C190.8936 (4)0.5584 (5)1.4279 (3)0.0601 (19)
H19A0.85240.51951.43540.072*
C200.9633 (4)0.5209 (5)1.4171 (3)0.0523 (17)
C211.0259 (4)0.5778 (5)1.4075 (3)0.0604 (19)
H21A1.07460.55201.40180.072*
C221.0147 (5)0.6738 (5)1.4067 (4)0.071 (2)
H22A1.05600.71241.39910.085*
C230.9246 (4)0.3560 (5)1.4198 (3)0.0612 (19)
H23A0.87110.37261.42170.073*
C240.9442 (4)0.2599 (5)1.4191 (3)0.0576 (19)
C250.8829 (5)0.1900 (6)1.4185 (5)0.089 (3)
H25A0.82960.20761.42000.107*
C260.9016 (6)0.0991 (7)1.4158 (5)0.105 (3)
H26A0.86060.05391.41420.126*
C270.9813 (5)0.0716 (6)1.4151 (4)0.083 (3)
H27A0.99260.00791.41320.099*
C281.0438 (4)0.1343 (5)1.4174 (4)0.0600 (19)
C291.0261 (4)0.2302 (5)1.4194 (3)0.0495 (16)
C301.1531 (5)0.0226 (5)1.4252 (4)0.086 (3)
H30A1.1104−0.01691.43330.129*
H30B1.20270.01881.45980.129*
H30C1.16560.00221.38750.129*
C311.6013 (7)0.4363 (7)1.7675 (4)0.122 (4)
H31A1.55650.42741.78660.183*
H31B1.62380.49841.77650.183*
H31C1.64460.39101.78400.183*
C321.5683 (6)0.4236 (6)1.6970 (4)0.079 (2)
C331.4863 (6)0.3989 (6)1.6687 (4)0.085 (3)
H33A1.44960.39041.69330.102*
C341.4576 (5)0.3865 (6)1.6047 (4)0.073 (2)
H34A1.40180.37141.58620.088*
C351.5109 (4)0.3963 (5)1.5688 (3)0.0514 (17)
C361.5935 (4)0.4198 (5)1.5956 (4)0.063 (2)
H36A1.63010.42661.57070.075*
C371.6216 (5)0.4334 (6)1.6600 (4)0.075 (2)
H37A1.67730.44931.67830.090*
C381.5238 (4)0.3633 (4)1.4624 (3)0.0523 (17)
H38A1.58190.36741.47650.063*
C391.4875 (4)0.3426 (4)1.3990 (3)0.0482 (16)
C401.5387 (4)0.3304 (5)1.3584 (4)0.064 (2)
H40A1.59640.33731.37390.077*
C411.5055 (5)0.3089 (6)1.2974 (4)0.072 (2)
H41A1.54030.30051.27140.087*
C421.4185 (5)0.2993 (5)1.2729 (3)0.0610 (19)
H42A1.39530.28651.23050.073*
C431.3680 (4)0.3090 (5)1.3120 (3)0.0522 (17)
C441.4000 (4)0.3316 (5)1.3758 (3)0.0483 (16)
C451.2416 (5)0.3000 (7)1.2278 (4)0.091 (3)
H45A1.28210.31121.20500.137*
H45B1.19930.34781.21780.137*
H45C1.21620.23971.21660.137*
C461.2340 (4)0.5040 (5)1.4736 (3)0.0591 (19)
C471.0439 (6)0.3648 (7)1.2736 (4)0.090 (3)
C481.3000 (4)0.1762 (5)1.5462 (3)0.0577 (18)
N11.4566 (4)0.1018 (4)1.4318 (3)0.0628 (16)
H1A1.41130.12621.43650.075*
N20.9766 (3)0.4219 (4)1.4181 (2)0.0510 (14)
H2A1.02580.40411.41750.061*
N31.4809 (3)0.3773 (4)1.5032 (3)0.0499 (14)
H3A1.42740.37481.48830.060*
N41.2184 (4)0.4345 (5)1.4465 (3)0.0754 (18)*
N51.1129 (5)0.3612 (5)1.3056 (4)0.094 (2)*
N61.2775 (4)0.2273 (5)1.5051 (3)0.0677 (17)*
S11.25218 (13)0.60404 (18)1.51067 (13)0.0996 (9)
S20.94976 (19)0.3689 (2)1.23046 (17)0.1467 (14)
S31.3324 (2)0.1029 (2)1.60350 (12)0.1132 (10)
O11.1632 (3)0.1444 (4)1.3004 (2)0.0752 (15)
O21.3015 (3)0.1459 (3)1.3889 (2)0.0561 (12)
O31.1243 (3)0.1167 (3)1.4178 (2)0.0674 (14)
O41.0848 (3)0.2913 (3)1.4208 (2)0.0595 (13)
O51.2824 (3)0.3020 (4)1.2938 (2)0.0641 (13)
O61.3500 (2)0.3412 (3)1.4114 (2)0.0538 (12)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Nd0.0425 (2)0.0534 (3)0.0489 (3)0.00325 (17)0.00670 (16)0.0035 (2)
C10.084 (7)0.122 (9)0.152 (11)0.005 (6)−0.028 (7)0.001 (8)
C20.073 (6)0.069 (6)0.104 (8)0.013 (5)−0.016 (6)−0.005 (6)
C30.053 (5)0.092 (7)0.134 (10)0.022 (5)0.000 (6)0.007 (7)
C40.066 (5)0.084 (6)0.088 (7)0.018 (4)0.019 (5)0.007 (5)
C50.072 (5)0.040 (4)0.078 (6)0.018 (4)0.016 (5)0.015 (4)
C60.061 (5)0.068 (5)0.063 (5)0.001 (4)0.009 (4)0.007 (4)
C70.091 (6)0.059 (5)0.083 (7)0.012 (5)0.001 (5)0.010 (5)
C80.074 (5)0.048 (5)0.073 (6)0.015 (4)0.023 (5)0.001 (4)
C90.092 (6)0.062 (5)0.058 (5)0.003 (4)0.029 (5)−0.010 (4)
C100.116 (8)0.086 (7)0.099 (8)0.001 (6)0.045 (7)−0.031 (6)
C110.140 (10)0.117 (9)0.074 (7)−0.021 (8)0.031 (7)−0.051 (6)
C120.118 (8)0.094 (7)0.073 (7)−0.016 (6)0.023 (6)−0.016 (6)
C130.084 (6)0.059 (5)0.050 (5)−0.002 (4)0.013 (4)−0.005 (4)
C140.076 (5)0.050 (4)0.057 (5)0.002 (4)0.018 (4)0.004 (4)
C150.079 (6)0.099 (7)0.086 (7)−0.020 (5)−0.029 (5)0.007 (6)
C160.122 (7)0.054 (5)0.085 (7)0.000 (5)0.003 (6)0.002 (5)
C170.078 (5)0.047 (5)0.049 (5)0.005 (4)−0.003 (4)−0.002 (4)
C180.074 (5)0.065 (5)0.067 (5)0.011 (4)0.019 (4)−0.001 (4)
C190.062 (4)0.055 (5)0.065 (5)−0.003 (3)0.021 (4)0.002 (4)
C200.055 (4)0.052 (4)0.049 (4)−0.006 (3)0.012 (3)−0.001 (3)
C210.056 (4)0.054 (5)0.066 (5)0.001 (4)0.009 (4)0.000 (4)
C220.063 (5)0.057 (5)0.083 (6)−0.006 (4)0.003 (4)0.011 (5)
C230.052 (4)0.060 (5)0.075 (5)−0.001 (4)0.023 (4)−0.006 (4)
C240.053 (4)0.063 (5)0.059 (5)−0.004 (3)0.018 (4)−0.002 (4)
C250.076 (5)0.072 (6)0.136 (9)−0.014 (5)0.056 (6)−0.012 (6)
C260.091 (7)0.070 (7)0.161 (10)−0.026 (5)0.046 (7)−0.023 (7)
C270.096 (6)0.047 (5)0.104 (7)−0.007 (5)0.027 (6)−0.002 (5)
C280.063 (4)0.036 (4)0.079 (6)−0.004 (3)0.017 (4)0.003 (4)
C290.056 (4)0.051 (4)0.042 (4)−0.012 (3)0.013 (3)0.003 (3)
C300.098 (6)0.042 (5)0.128 (8)0.020 (4)0.045 (6)0.014 (5)
C310.189 (11)0.114 (9)0.051 (6)−0.040 (8)0.012 (7)−0.017 (6)
C320.111 (7)0.070 (6)0.049 (5)−0.015 (5)0.013 (5)−0.015 (4)
C330.112 (7)0.090 (7)0.064 (6)−0.031 (5)0.042 (6)−0.018 (5)
C340.074 (5)0.088 (6)0.062 (6)−0.017 (4)0.026 (5)−0.017 (5)
C350.057 (4)0.046 (4)0.050 (4)−0.004 (3)0.011 (4)−0.007 (3)
C360.057 (4)0.072 (5)0.060 (5)−0.013 (4)0.018 (4)−0.006 (4)
C370.075 (5)0.077 (6)0.063 (6)−0.010 (4)0.001 (5)−0.022 (5)
C380.048 (4)0.053 (4)0.058 (5)0.003 (3)0.018 (4)−0.004 (4)
C390.050 (4)0.045 (4)0.050 (4)−0.002 (3)0.015 (3)0.003 (3)
C400.052 (4)0.074 (5)0.071 (6)−0.003 (4)0.024 (4)−0.016 (4)
C410.077 (5)0.088 (6)0.061 (6)−0.002 (4)0.034 (5)−0.011 (5)
C420.074 (5)0.065 (5)0.042 (4)−0.003 (4)0.013 (4)0.005 (4)
C430.060 (4)0.054 (4)0.040 (4)−0.007 (3)0.009 (3)0.002 (3)
C440.053 (4)0.046 (4)0.046 (4)−0.002 (3)0.013 (3)0.006 (3)
C450.078 (6)0.133 (8)0.054 (5)−0.017 (5)0.001 (4)0.025 (5)
C460.045 (4)0.064 (5)0.066 (5)−0.010 (3)0.012 (4)−0.007 (4)
C470.079 (6)0.102 (7)0.080 (7)0.013 (5)0.007 (5)−0.003 (5)
C480.068 (4)0.064 (5)0.043 (4)0.012 (4)0.018 (4)−0.003 (4)
N10.062 (4)0.050 (4)0.074 (5)0.010 (3)0.016 (4)0.003 (4)
N20.044 (3)0.047 (3)0.062 (4)0.005 (3)0.014 (3)0.003 (3)
N30.044 (3)0.052 (3)0.052 (4)0.000 (2)0.010 (3)−0.006 (3)
S10.0686 (13)0.0964 (17)0.145 (2)−0.0332 (12)0.0477 (15)−0.0558 (17)
S20.094 (2)0.142 (3)0.161 (3)0.0396 (18)−0.038 (2)−0.016 (2)
S30.158 (3)0.122 (2)0.0708 (17)0.066 (2)0.0515 (17)0.0365 (16)
O10.073 (3)0.082 (4)0.059 (4)−0.009 (3)−0.002 (3)0.003 (3)
O20.059 (3)0.061 (3)0.044 (3)0.010 (2)0.007 (2)−0.003 (2)
O30.066 (3)0.048 (3)0.089 (4)0.009 (2)0.021 (3)0.005 (3)
O40.051 (3)0.046 (3)0.084 (4)−0.001 (2)0.023 (3)−0.002 (3)
O50.060 (3)0.084 (4)0.043 (3)−0.012 (2)0.005 (2)0.006 (3)
O60.048 (2)0.069 (3)0.046 (3)−0.002 (2)0.015 (2)−0.009 (2)

Geometric parameters (Å, °)

Nd—O42.375 (4)C23—H23A0.9300
Nd—O62.388 (4)C24—C251.421 (10)
Nd—O22.393 (4)C24—C291.423 (9)
Nd—N52.489 (8)C25—C261.336 (12)
Nd—N62.517 (7)C25—H25A0.9300
Nd—N42.530 (7)C26—C271.385 (12)
Nd—O12.742 (5)C26—H26A0.9300
Nd—O52.778 (5)C27—C281.359 (10)
Nd—O32.843 (5)C27—H27A0.9300
C1—C21.530 (12)C28—O31.357 (8)
C1—H1B0.9600C28—C291.400 (9)
C1—H1C0.9600C29—O41.302 (7)
C1—H1D0.9600C30—O31.417 (8)
C2—C31.366 (12)C30—H30A0.9600
C2—C71.397 (12)C30—H30B0.9600
C3—C41.376 (12)C30—H30C0.9600
C3—H3B0.9300C31—C321.518 (10)
C4—C51.380 (10)C31—H31A0.9600
C4—H4A0.9300C31—H31B0.9600
C5—C61.379 (10)C31—H31C0.9600
C5—N11.405 (9)C32—C371.369 (10)
C6—C71.363 (10)C32—C331.380 (11)
C6—H6A0.9300C33—C341.379 (10)
C7—H7A0.9300C33—H33A0.9300
C8—N11.289 (9)C34—C351.350 (9)
C8—C91.413 (10)C34—H34A0.9300
C8—H8A0.9300C35—C361.379 (9)
C9—C141.403 (10)C35—N31.427 (8)
C9—C101.435 (11)C36—C371.388 (9)
C10—C111.358 (13)C36—H36A0.9300
C10—H10A0.9300C37—H37A0.9300
C11—C121.380 (13)C38—N31.311 (7)
C11—H11A0.9300C38—C391.400 (9)
C12—C131.373 (11)C38—H38A0.9300
C12—H12A0.9300C39—C401.409 (9)
C13—O11.358 (9)C39—C441.410 (8)
C13—C141.412 (10)C40—C411.347 (10)
C14—O21.307 (8)C40—H40A0.9300
C15—O11.450 (8)C41—C421.403 (10)
C15—H15A0.9600C41—H41A0.9300
C15—H15B0.9600C42—C431.369 (9)
C15—H15C0.9600C42—H42A0.9300
C16—C171.503 (10)C43—O51.371 (8)
C16—H16A0.9600C43—C441.403 (9)
C16—H16B0.9600C44—O61.301 (7)
C16—H16C0.9600C45—O51.433 (8)
C17—C181.374 (10)C45—H45A0.9600
C17—C221.380 (10)C45—H45B0.9600
C18—C191.391 (10)C45—H45C0.9600
C18—H18A0.9300C46—N41.150 (8)
C19—C201.355 (9)C46—S11.630 (8)
C19—H19A0.9300C47—N51.171 (10)
C20—C211.379 (9)C47—S21.594 (9)
C20—N21.426 (8)C48—N61.145 (8)
C21—C221.379 (10)C48—S31.617 (8)
C21—H21A0.9300N1—H1A0.8600
C22—H22A0.9300N2—H2A0.8600
C23—N21.284 (8)N3—H3A0.8600
C23—C241.408 (9)
O4—Nd—O6143.38 (15)C21—C22—C17122.1 (7)
O4—Nd—O2133.12 (15)C21—C22—H22A119.0
O6—Nd—O274.67 (15)C17—C22—H22A119.0
O4—Nd—N573.0 (2)N2—C23—C24123.4 (6)
O6—Nd—N5110.2 (2)N2—C23—H23A118.3
O2—Nd—N5129.1 (2)C24—C23—H23A118.3
O4—Nd—N686.67 (18)C23—C24—C25120.9 (7)
O6—Nd—N679.11 (18)C23—C24—C29120.9 (6)
O2—Nd—N673.77 (18)C25—C24—C29118.2 (7)
N5—Nd—N6156.4 (2)C26—C25—C24120.3 (8)
O4—Nd—N473.90 (18)C26—C25—H25A119.8
O6—Nd—N470.59 (17)C24—C25—H25A119.8
O2—Nd—N4139.96 (18)C25—C26—C27120.6 (8)
N5—Nd—N482.2 (2)C25—C26—H26A119.7
N6—Nd—N480.6 (2)C27—C26—H26A119.7
O4—Nd—O198.57 (16)C28—C27—C26122.4 (8)
O6—Nd—O1117.78 (15)C28—C27—H27A118.8
O2—Nd—O159.79 (16)C26—C27—H27A118.8
N5—Nd—O175.5 (2)O3—C28—C27128.3 (7)
N6—Nd—O1120.39 (18)O3—C28—C29113.2 (6)
N4—Nd—O1157.76 (19)C27—C28—C29118.5 (7)
O4—Nd—O5142.12 (16)O4—C29—C28119.4 (6)
O6—Nd—O559.78 (14)O4—C29—C24120.7 (6)
O2—Nd—O570.97 (15)C28—C29—C24119.9 (6)
N5—Nd—O569.7 (2)O3—C30—H30A109.5
N6—Nd—O5131.17 (17)O3—C30—H30B109.5
N4—Nd—O5106.50 (18)H30A—C30—H30B109.5
O1—Nd—O566.39 (15)O3—C30—H30C109.5
O4—Nd—O358.38 (13)H30A—C30—H30C109.5
O6—Nd—O3142.73 (15)H30B—C30—H30C109.5
O2—Nd—O375.00 (15)C32—C31—H31A109.5
N5—Nd—O3105.6 (2)C32—C31—H31B109.5
N6—Nd—O372.00 (18)H31A—C31—H31B109.5
N4—Nd—O3125.27 (17)C32—C31—H31C109.5
O1—Nd—O361.95 (15)H31A—C31—H31C109.5
O5—Nd—O3127.32 (14)H31B—C31—H31C109.5
C2—C1—H1B109.5C37—C32—C33118.4 (8)
C2—C1—H1C109.5C37—C32—C31119.6 (8)
H1B—C1—H1C109.5C33—C32—C31122.0 (9)
C2—C1—H1D109.5C34—C33—C32121.2 (8)
H1B—C1—H1D109.5C34—C33—H33A119.4
H1C—C1—H1D109.5C32—C33—H33A119.4
C3—C2—C7117.3 (9)C35—C34—C33119.8 (8)
C3—C2—C1122.1 (10)C35—C34—H34A120.1
C7—C2—C1120.7 (11)C33—C34—H34A120.1
C2—C3—C4122.3 (9)C34—C35—C36120.6 (7)
C2—C3—H3B118.8C34—C35—N3118.6 (6)
C4—C3—H3B118.8C36—C35—N3120.8 (6)
C3—C4—C5119.2 (9)C35—C36—C37119.3 (7)
C3—C4—H4A120.4C35—C36—H36A120.3
C5—C4—H4A120.4C37—C36—H36A120.3
C6—C5—C4119.8 (8)C32—C37—C36120.8 (7)
C6—C5—N1117.6 (7)C32—C37—H37A119.6
C4—C5—N1122.5 (8)C36—C37—H37A119.6
C7—C6—C5119.8 (8)N3—C38—C39123.9 (6)
C7—C6—H6A120.1N3—C38—H38A118.0
C5—C6—H6A120.1C39—C38—H38A118.0
C6—C7—C2121.6 (9)C38—C39—C40119.9 (6)
C6—C7—H7A119.2C38—C39—C44120.4 (6)
C2—C7—H7A119.2C40—C39—C44119.7 (6)
N1—C8—C9122.6 (7)C41—C40—C39121.1 (7)
N1—C8—H8A118.7C41—C40—H40A119.5
C9—C8—H8A118.7C39—C40—H40A119.5
C14—C9—C8120.7 (7)C40—C41—C42120.3 (7)
C14—C9—C10118.0 (8)C40—C41—H41A119.9
C8—C9—C10121.3 (8)C42—C41—H41A119.9
C11—C10—C9120.7 (9)C43—C42—C41119.4 (7)
C11—C10—H10A119.6C43—C42—H42A120.3
C9—C10—H10A119.6C41—C42—H42A120.3
C10—C11—C12120.7 (9)C42—C43—O5125.0 (6)
C10—C11—H11A119.7C42—C43—C44122.2 (6)
C12—C11—H11A119.7O5—C43—C44112.8 (6)
C13—C12—C11120.8 (10)O6—C44—C43120.4 (6)
C13—C12—H12A119.6O6—C44—C39122.2 (6)
C11—C12—H12A119.6C43—C44—C39117.4 (6)
O1—C13—C12126.4 (8)O5—C45—H45A109.5
O1—C13—C14113.4 (7)O5—C45—H45B109.5
C12—C13—C14120.1 (8)H45A—C45—H45B109.5
O2—C14—C9122.0 (7)O5—C45—H45C109.5
O2—C14—C13118.4 (7)H45A—C45—H45C109.5
C9—C14—C13119.6 (7)H45B—C45—H45C109.5
O1—C15—H15A109.5N4—C46—S1177.7 (7)
O1—C15—H15B109.5N5—C47—S2179.4 (11)
H15A—C15—H15B109.5N6—C48—S3179.1 (7)
O1—C15—H15C109.5C8—N1—C5128.6 (7)
H15A—C15—H15C109.5C8—N1—H1A115.7
H15B—C15—H15C109.5C5—N1—H1A115.7
C17—C16—H16A109.5C23—N2—C20128.4 (6)
C17—C16—H16B109.5C23—N2—H2A115.8
H16A—C16—H16B109.5C20—N2—H2A115.8
C17—C16—H16C109.5C38—N3—C35128.9 (6)
H16A—C16—H16C109.5C38—N3—H3A115.6
H16B—C16—H16C109.5C35—N3—H3A115.6
C18—C17—C22117.5 (7)C46—N4—Nd169.5 (6)
C18—C17—C16121.3 (7)C47—N5—Nd145.5 (7)
C22—C17—C16121.3 (7)C48—N6—Nd156.7 (6)
C17—C18—C19121.4 (7)C13—O1—C15118.2 (7)
C17—C18—H18A119.3C13—O1—Nd115.5 (4)
C19—C18—H18A119.3C15—O1—Nd126.1 (5)
C20—C19—C18119.5 (7)C14—O2—Nd127.0 (4)
C20—C19—H19A120.2C28—O3—C30118.4 (6)
C18—C19—H19A120.2C28—O3—Nd114.2 (4)
C19—C20—C21120.8 (7)C30—O3—Nd127.1 (4)
C19—C20—N2121.5 (6)C29—O4—Nd130.7 (4)
C21—C20—N2117.6 (6)C43—O5—C45117.5 (6)
C20—C21—C22118.7 (7)C43—O5—Nd113.7 (4)
C20—C21—H21A120.6C45—O5—Nd128.6 (4)
C22—C21—H21A120.6C44—O6—Nd126.7 (4)
C7—C2—C3—C40.6 (14)O5—Nd—N5—C47131.5 (13)
C1—C2—C3—C4−178.2 (9)O3—Nd—N5—C476.9 (13)
C2—C3—C4—C5−0.5 (14)O4—Nd—N6—C4893.5 (14)
C3—C4—C5—C60.1 (12)O6—Nd—N6—C48−120.4 (14)
C3—C4—C5—N1177.5 (7)O2—Nd—N6—C48−43.4 (14)
C4—C5—C6—C70.0 (11)N5—Nd—N6—C48123.6 (14)
N1—C5—C6—C7−177.5 (7)N4—Nd—N6—C48167.7 (14)
C5—C6—C7—C20.2 (12)O1—Nd—N6—C48−4.5 (15)
C3—C2—C7—C6−0.5 (13)O5—Nd—N6—C48−88.5 (14)
C1—C2—C7—C6178.4 (8)O3—Nd—N6—C4835.7 (14)
N1—C8—C9—C140.5 (12)C12—C13—O1—C1511.3 (12)
N1—C8—C9—C10179.5 (8)C14—C13—O1—C15−170.5 (7)
C14—C9—C10—C110.1 (13)C12—C13—O1—Nd−163.8 (7)
C8—C9—C10—C11−178.9 (9)C14—C13—O1—Nd14.4 (8)
C9—C10—C11—C120.8 (16)O4—Nd—O1—C13−153.4 (5)
C10—C11—C12—C13−0.5 (16)O6—Nd—O1—C1331.3 (5)
C11—C12—C13—O1177.3 (9)O2—Nd—O1—C13−18.0 (4)
C11—C12—C13—C14−0.8 (13)N5—Nd—O1—C13136.8 (5)
C8—C9—C14—O2−2.0 (11)N6—Nd—O1—C13−62.2 (5)
C10—C9—C14—O2179.0 (7)N4—Nd—O1—C13138.5 (6)
C8—C9—C14—C13177.7 (7)O5—Nd—O1—C1363.0 (5)
C10—C9—C14—C13−1.3 (11)O3—Nd—O1—C13−106.3 (5)
O1—C13—C14—O23.0 (10)O4—Nd—O1—C1532.0 (6)
C12—C13—C14—O2−178.7 (7)O6—Nd—O1—C15−143.3 (6)
O1—C13—C14—C9−176.6 (7)O2—Nd—O1—C15167.4 (6)
C12—C13—C14—C91.7 (11)N5—Nd—O1—C15−37.8 (6)
C22—C17—C18—C19−0.4 (12)N6—Nd—O1—C15123.2 (6)
C16—C17—C18—C19−179.8 (7)N4—Nd—O1—C15−36.1 (8)
C17—C18—C19—C20−0.3 (12)O5—Nd—O1—C15−111.6 (6)
C18—C19—C20—C211.8 (11)O3—Nd—O1—C1579.1 (6)
C18—C19—C20—N2178.8 (6)C9—C14—O2—Nd155.3 (5)
C19—C20—C21—C22−2.5 (11)C13—C14—O2—Nd−24.4 (9)
N2—C20—C21—C22−179.6 (6)O4—Nd—O2—C1494.2 (6)
C20—C21—C22—C171.8 (12)O6—Nd—O2—C14−113.8 (5)
C18—C17—C22—C21−0.4 (12)N5—Nd—O2—C14−10.0 (6)
C16—C17—C22—C21179.0 (7)N6—Nd—O2—C14163.3 (6)
N2—C23—C24—C25−177.4 (8)N4—Nd—O2—C14−144.3 (5)
N2—C23—C24—C293.1 (12)O1—Nd—O2—C1422.2 (5)
C23—C24—C25—C26177.8 (9)O5—Nd—O2—C14−51.0 (5)
C29—C24—C25—C26−2.7 (14)O3—Nd—O2—C1488.1 (5)
C24—C25—C26—C271.8 (16)C27—C28—O3—C30−9.3 (12)
C25—C26—C27—C280.1 (16)C29—C28—O3—C30170.8 (7)
C26—C27—C28—O3179.2 (9)C27—C28—O3—Nd165.9 (7)
C26—C27—C28—C29−0.9 (14)C29—C28—O3—Nd−14.0 (8)
O3—C28—C29—O40.8 (10)O4—Nd—O3—C2815.7 (5)
C27—C28—C29—O4−179.1 (7)O6—Nd—O3—C28154.0 (4)
O3—C28—C29—C24179.9 (6)O2—Nd—O3—C28−169.5 (5)
C27—C28—C29—C240.0 (11)N5—Nd—O3—C28−42.4 (5)
C23—C24—C29—O40.4 (11)N6—Nd—O3—C28113.0 (5)
C25—C24—C29—O4−179.1 (7)N4—Nd—O3—C2849.1 (5)
C23—C24—C29—C28−178.7 (7)O1—Nd—O3—C28−106.1 (5)
C25—C24—C29—C281.8 (11)O5—Nd—O3—C28−118.4 (5)
C37—C32—C33—C34−1.6 (14)O4—Nd—O3—C30−169.6 (7)
C31—C32—C33—C34−179.1 (9)O6—Nd—O3—C30−31.3 (7)
C32—C33—C34—C351.7 (13)O2—Nd—O3—C305.2 (6)
C33—C34—C35—C36−0.9 (12)N5—Nd—O3—C30132.3 (6)
C33—C34—C35—N3176.1 (7)N6—Nd—O3—C30−72.3 (6)
C34—C35—C36—C370.0 (11)N4—Nd—O3—C30−136.2 (6)
N3—C35—C36—C37−176.9 (7)O1—Nd—O3—C3068.6 (6)
C33—C32—C37—C360.8 (13)O5—Nd—O3—C3056.2 (6)
C31—C32—C37—C36178.4 (8)C28—C29—O4—Nd18.9 (9)
C35—C36—C37—C320.0 (12)C24—C29—O4—Nd−160.2 (5)
N3—C38—C39—C40178.8 (6)O6—Nd—O4—C29−155.9 (5)
N3—C38—C39—C44−2.8 (10)O2—Nd—O4—C29−25.1 (7)
C38—C39—C40—C41178.9 (7)N5—Nd—O4—C29103.0 (6)
C44—C39—C40—C410.5 (11)N6—Nd—O4—C29−89.1 (6)
C39—C40—C41—C420.7 (12)N4—Nd—O4—C29−170.3 (6)
C40—C41—C42—C43−2.1 (12)O1—Nd—O4—C2931.1 (6)
C41—C42—C43—O5179.5 (7)O5—Nd—O4—C2993.3 (6)
C41—C42—C43—C442.2 (11)O3—Nd—O4—C29−18.3 (5)
C42—C43—C44—O6179.3 (6)C42—C43—O5—C45−11.0 (10)
O5—C43—C44—O61.7 (9)C44—C43—O5—C45166.5 (6)
C42—C43—C44—C39−1.0 (10)C42—C43—O5—Nd163.6 (6)
O5—C43—C44—C39−178.6 (6)C44—C43—O5—Nd−18.9 (7)
C38—C39—C44—O60.9 (10)O4—Nd—O5—C43160.4 (4)
C40—C39—C44—O6179.4 (6)O6—Nd—O5—C4320.6 (4)
C38—C39—C44—C43−178.8 (6)O2—Nd—O5—C43−62.4 (4)
C40—C39—C44—C43−0.3 (10)N5—Nd—O5—C43150.5 (5)
C9—C8—N1—C5−173.3 (7)N6—Nd—O5—C43−16.3 (5)
C6—C5—N1—C8−160.0 (7)N4—Nd—O5—C4375.6 (5)
C4—C5—N1—C822.5 (11)O1—Nd—O5—C43−126.9 (5)
C24—C23—N2—C20178.3 (7)O3—Nd—O5—C43−115.0 (4)
C19—C20—N2—C2310.6 (11)O4—Nd—O5—C45−25.8 (7)
C21—C20—N2—C23−172.3 (7)O6—Nd—O5—C45−165.6 (7)
C39—C38—N3—C35178.2 (6)O2—Nd—O5—C45111.5 (6)
C34—C35—N3—C38−164.5 (7)N5—Nd—O5—C45−35.7 (6)
C36—C35—N3—C3812.5 (10)N6—Nd—O5—C45157.5 (6)
O4—Nd—N4—C46150 (3)N4—Nd—O5—C45−110.6 (6)
O6—Nd—N4—C46−21 (3)O1—Nd—O5—C4546.9 (6)
O2—Nd—N4—C4610 (4)O3—Nd—O5—C4558.8 (7)
N5—Nd—N4—C46−136 (3)C43—C44—O6—Nd22.3 (9)
N6—Nd—N4—C4661 (3)C39—C44—O6—Nd−157.3 (5)
O1—Nd—N4—C46−137 (3)O4—Nd—O6—C44−160.7 (5)
O5—Nd—N4—C46−70 (3)O2—Nd—O6—C4454.3 (5)
O3—Nd—N4—C46121 (3)N5—Nd—O6—C44−72.3 (5)
O4—Nd—N5—C47−42.1 (12)N6—Nd—O6—C44130.2 (5)
O6—Nd—N5—C47176.5 (12)N4—Nd—O6—C44−146.0 (5)
O2—Nd—N5—C4790.1 (13)O1—Nd—O6—C4411.5 (5)
N6—Nd—N5—C47−73.7 (15)O5—Nd—O6—C44−22.3 (5)
N4—Nd—N5—C47−117.6 (13)O3—Nd—O6—C4490.8 (5)
O1—Nd—N5—C4761.8 (13)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O20.861.862.566 (7)138
N2—H2A···O40.861.872.576 (6)138
N3—H3A···O60.861.892.589 (7)137
C38—H38A···S1i0.932.723.633 (6)166

Symmetry codes: (i) −x+3, −y+1, −z+3.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2653).

References

  • Bruker (2006). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Li, H.-Q., Xian, H.-D., Liu, J.-F. & Zhao, G.-L. (2008). Acta Cryst. E64, m1593–m1594. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, G. & Chang, J.-C. (1994). Synth. React. Inorg. Met. Org. Chem.24, 623–627.
  • Xian, H.-D., Liu, J.-F., Li, H.-Q. & Zhao, G.-L. (2008). Acta Cryst. E64, m1422. [PMC free article] [PubMed]
  • Zhao, G.-L., Shi, X. & Ng, S. W. (2007). Acta Cryst. E63, m267–m268.

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